


Oh Man.

by Silly_boiiiiii



Category: IT Crowd
Genre: Cute, F/M, Happy Ending, Healthy Relationships, Smut
Language: English
Status: Completed
Published: 2020-09-07
Updated: 2020-09-07
Packaged: 2021-03-07 04:07:47
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 4,997
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26346850
Author URL: https://archiveofourown.org/users/Silly_boiiiiii/pseuds/Silly_boiiiiii
Summary: Roy had always liked Jen. Now, seemingly at the same time, they realised the feelings were mutual. Would it end well?
Relationships: Jen Barber/Roy Trenneman
Kudos: 7





	1. Chapter 1

**Author's Note:**

> Thank you so much for reading!!

It was late, and frankly it was starting to show. Either way, curiosity still got the better of Jen. She had never seen this place before. Almost eight years and she had never been to Moss’s house before. And boy, did it live up to what she expected. About half of it was a foreign language to her. What were these little figurines? And these posters? She had no idea what any of it meant.

How she ended up here was more of a mystery. Only a week ago, neither her nor Roy had any idea who Pam was, and now, she was his fiance. This lady seemed very nice, if not a few years off of retirement age. A gold digger? That had to be a low blow; the I.T department weren’t exactly low earners, Douglas had forgotten to hire someone to balance the books a few years previous and the wages got silly for a while. It was just bizarre to them all. Jen had lost Roy a few hours ago, and had since been lost in nerd city. The new normal had been to just nod along politely as they all talked on, ogling at her tits. In hindsight she should have probably asked them if they knew what I.T meant. There’s always another day.

Finally, it seemed to only be Moss and Jen left in the flat, which by now was littered with all sorts. She would offer to clear it up, but she had already served as personality control for most of the evening.

“Moss?” Jen asked loudly so that he would hear her from the other room.

“Yes, Jen?” He replied, equally as loudly.

“Am I alright to go home now?” She asked back, wanting to avoid the cleanup.

“Yep. Oh, before I forget to ask, I won’t be here for a couple of weeks.” He said, sounding anxious.

“Okay. Of course, the wedding. Have a good time. Where are you two going?” Jen tried to finish the conversation without appearing rude.

“We’re going to a convention.”

And with that, Jen left abruptly.

The next morning, when Jen walked into the office, she already found Roy at his desk, as if it were just a normal morning.

“Morning Roy.” Jen called out, with a lack of a reply that would frustrated her. 

“Morning Roy.” She repeated herself, and he finally looked up.

“Oh, hi Jen.” 

“I didn’t see you last night. Did you leave early?”

“Yeah. I was going on a date. You know what they are, right?”

She laughed as a courtesy, before walking up closer to the desk, stopping behind the computer monitor.

“Was she nice?”

“Oh yeah, lovely. Nice sense of humour. And, guess what?”

“What?”

“She doesn’t work here.”

“That must be a first.”

They both laugh more genuinely this time. She had always felt a warmth toward him, not romantic or anything, just that she felt something...No. 

“Where’s the bride to be, then?” Roy finally enquired, finally looking up from his computer.

“You do know the wedding is tomorrow, right?”

“What?”

“Ten. All Saint’s opposite King’s Avenue.”

“That’s remarkably normal.”

“Just...Look nice, alright?”

“You’re not my mother.”

For the rest of the day, Jen thought about the wedding. Even that thought was insane to her. It was all just so quick. She wanted to ask Roy, but he seemed to be in some kind of mood. He was always different after a date, but this was overboard. Usually it was just some kind of style change but this was just...Bleak. He was hiding it as well. It was weird. Very weird. Trying not to think too much about it, Jen continued with her work. The two worked silently for the rest of the day, as actual offices do. Were they finally becoming normal?

At the end of the day, they both left the office at the same time, without saying anything, got the same lift upstairs, walked the same way for a few streets and only really acknowledged each other when Jen had to walk away back towards her flat. This was weird, too weird?

When the wedding came, it was fairly orthodox. This Pam lady seemed to be extremely traditional, and now Moss was shackled up. No reception, no cake cutting, no sing-song and dance. They were just gone, like that. Jen went back to work, not thinking to change out of the dress. It was nice, and deserved a little outing. She just had to avoid Douglas, now. Didn’t want to start another sex scandal. When Roy came back, it was a much different story. He pretty much threw off the clothes, quickly adorning his casual wear and throwing the suit into the corner. 

“That shirt is gonna get crinkled up in there.”

Jen’s voice scared Roy, who thought that he was alone. He shrugged his shoulders, before sitting back down in his chair anyway.

“We’re not going to be doing this for the next three weeks, are we Roy?”

There was still nothing coming from him.

“Did you just watch me get dressed?” He finally asked, slightly distressed.

“It’s nothing I haven’t seen before.” 

“Oh, that makes it so much better.”

“Stop being a child.”

He stuck his tongue out before getting back to his work. Finally, she walked out of her office and into theirs. 

“Right, what’s wrong?”

“I’m just worried about Moss.”

She smiled meekly back at him. To be honest, she felt the same way. This was exrremely weird, even for him. Something had to be up.


	2. What Was This?

Day four of a department without Moss. By this point, the catchphrase had become etched into Jen’s brain. Ironically, she probably needed to turn it off and on again. Things had calmed between the two of them, although it was still weirdly awkward. Finding Roy’s tie in her office, she walked in, and tried to hand it back to him.

“I hate ties.” He remarked, taking it in his hands.

“Why?”

“They’re just so...Ugh. That was one of my requirements for working here. I didn’t have to wear one of those things.”

“They’re professional.”

“Ugly.”

“Roy.”

“What, they are. Come on, put that on right now and tell me that isn’t ugly.”

Jen paused, and they both quickly came to the same realisation.

“You don’t know how to tie that, do you?”

Shaking her head, she laughed a little bit. This was stupid. Roy rolled his eyes and stood up from his desk, walking over to face her.

“Stay still.” He said surprisingly softly, putting it around her neck. He muttered away to himself for a minute, before completing the finished product and turning her around to face a mirror.

“See. Ugly.”

“I’m ugly, am I?” Jen remarked, mostly in a joking fashion. Quickly, Roy tried to dig himself out of the pit that he had gotten himself into but with little success.

“No, no. You’re beautiful. But that…” His joking shudder made them both laugh, and for a minute they stood, one behind the other, looking into the mirror. Roy put his hands on her shoulders, presumably to walk away, but found his feet glued to the floor. For the first time since she had started working there, all suddenly became clear. The crush was mutual. Roy moved his hands down to her shoulders, and began to make silly faces into the mirror. Their laughter temporarily replaced any tension that may have been growing. Finally, he reached around and loosened the tie, taking it off. At this point, both of them knew. It just seemed far too early to do anything about it. 

“Douglas was talking about having a work thing later, at the pub.” Jen finally said something, and they both tried to resume normal activity.

“Oh. Fun.”

“Come on, please go.”

“Really?”

“For me?”

“Fine.”

“Oh, and it’s a formal dress code.”

“For the pub?” Roy asked in disgust.

“Just don’t turn up in that.”

Jen spent the rest of the day in her office, pondering her predicament. This wasn’t the time. But then again, when was the time? She knew that Roy liked her, but she had never felt the same way until a few weeks ago. It just didn’t sit right with her. He had gone on a date. He hadn’t stopped going on dates since she started working there, pretty much. They had agreed that she meet him at his house, so she set off for there straight from work. She had already packed some clothes, and his house was closer to the pub, anyway. Walking there, that was all her mind was thinking about. 

Reaching Roy’s house, she rang the doorbell and waited for a few seconds, before Roy emerged from the other side of the door. He looked...Nice. Like, really nice. He had a nice shirt on and looked genuinely quite smart. 

“Sorry, can I use your bathroom? I need to change.”

“Sure, go ahead.”

She awkwardly walked past him and into his bathroom, which had the look of a male all over it. It was just...Awful. However, she tried to avoid it and she eventually slipped into the best dress that she owned and touched up her makeup as well, before leaving. Roy looked as stunned as she did when she saw him.

“Listen, before we go-”

“I know.”

Not anticipating this reply, Roy was unsure on how to proceed. 

“Can we talk about this some other time?” Jen stated, eagerly walking out of the door.

“Yeah, fine.”

The party looked as expected, just slightly more formal. Douglas had booked the entire place out, and people had already formed little groups together and had begun to chat. The pair split, and started talking to different groups of people. Jen felt slightly bad when she did this, but had an image to maintain with the rest of the company. Roy would find Richmond or something. It would be fine.

They met a few hours and a few drinks later on the dance floor, awkwardly dancing to some upbeat dance anthem. And then, the music slowed. Once again, this had quickly evolved into awkwardness. They adopted some form of crude dance hold and began to slowly get more comfortable. Eventually, Jen rested her head against Roy’s chest and they continued to dance slowly for the rest of the song. Roy knew that this was getting bad but at this point sort of wanted to see how much worse it would get.

After the dance, Roy bought them both drinks and they retreated to the last table left empty in the pub, right in the corner. Jen sat next to him and gave him a beaming smile, leaving Roy wondering how much of this was the booze. He decided to shoot his shot in the most cowardly way he could think of, slipping his hands into hers underneath the table. She gripped his hand back, and they suddenly felt like teenagers again. 

“I love you, Roy.” Jen said quietly in his ear, nowhere near loud enough for the rest of the pub to hear her.

“No, the wine loves me.”

“No, no. I...I love you.” 

“Let’s take you home now, shall we?”

Pretty quickly he realized that he had to help her home, and the two basically stumbled into her front door, where she promptly threw up. After laughing at the slightly amusing situation, Roy almost carried her through to her bedroom and put her down into her bed, tucking up the sheets. Then, he left to deal with the sick, something he was slightly more equipped to do than people telling him that they love him. Finally, he resigned himself to sitting on the chair in the corner of her bedroom, making sure that nothing stupid happened.

“I love you too.” He said in a barely audible voice, smiling to himself. How in the hell was he going to get himself out of this one.


	3. Something Different

The morning after the party, a day that was luckily a Saturday for them both, the smell of coffee woke Jen up. After the initial shock of seeing Roy in her bedroom, the headache hit. That was a lot of alcohol. His eyes were kind, which was an unusual sight. He was still in his clothes from last night as well, which looked even better on him after a while.

“Did I tell you that I loved you last night?”

“Yeah.”

“Fuck.”

They both laughed to themselves for a minute.

“And no, we didn’t have sex.” Roy added afterwards, running his hands through his hair.

“Thank you for doing all this. I do love you, you know. Just probably not in the way that I said last night.” She knew that she was lying. 

“I figured. Listen, can we talk now about it?”

“Really, Roy?”

“I...I need to talk about it. We don’t have to do anything about it, I get that. But we can’t just lie to each other about it.”

“What do you want to do?”

“What I’ve wanted to do since the minute you walked into our office.”

“And what’s that?”

“You know.”

“No, I don’t.”

“Tell me.”

“I don’t need to tell you.”

“Show me then.”

He obliged, touching the side of her face and kissing her gently. Surprised but not disgusted, Jen pulled him back in and kissed him more. He sat down on the bed slowly and then they began to kiss further, getting more and more adventurous with every second. This wasn’t just proving a point anymore. Eventually, Roy backed away slightly. 

“I’ll be back later. I want to do this properly.”

“Okay.” Jen smiled.

Not knowing what to do with his hands, Roy shooted finger guns at Jen awkwardly before walking away. He could not believe he just did that. Something was weird, he could feel it. It felt neither good nor bad just...Different. Maybe it was the panic? There was definitely panic. He walked home in a sweat, thinking of her. Usually, the feeling around girls was mostly sexual. He wasn’t exactly one to objectify women, but there was never any stakes. If he decided that he didn’t like them anymore, he could go back to work, to Moss and Jen. Who was he kidding? As much as he loved Moss it was different. This was real.

After what seemed like an eternity, Roy finally changed out of the clothes that he had been wearing since the night previous. He looked at himself in the mirror, shirtless. Was this really the guy she liked? Fuck, he thought. The shirt smelt disgusting, it had touched way more of Jen’s sick than he was comfortable with and had a few stains on it. He liked that shirt as well. He eventually managed to calm himself down and think about what he wanted to do that night. I mean, this was his plan. His stupid, stupid plan. But then again, this was different. It was weird. He didn’t just like the idea of falling in love with her, but staying in love with her. As annoying as she was, that was endearing. Cute. Hot. 

Plan. He needed a plan. Fuck her brains out wasn’t a good enough plan. Guitar Hero? Oh. Oh no. He almost winced at the idea. As much as that was amazing, this was different. A date. But then again, it was a date with Jen. Maybe some more of what they always did was what she actually wanted? No, he didn’t want to have sex with her yet. This wasn’t the night. His mind continued to scarper. Finally, he came up with an idea. Something that reminded them of the early days. A trip down memory lane. No, not some sex pants or making their boss jump out of a window. He wanted to do something special. 

When Roy finally arrived, she did not expect Roy to look so smart. It looked eerily similar to his funeral attire, but she didn’t want to say anything. He looked as if he were about to say ‘ta da’, although luckily that was not the case. The finger guns were already dire. They began to walk down the street, and eventually reached a bar that seemed familiar to Jen.

“Have I been here before?”

“Yeah. Come on, think.”

“I don’t know. Tell me.”

“This is where I tried to make you say that you loved me in front of all of those snobs.”

“Where Moss was my husband?”

“We’ll forget about that bit. It’s great, isn’t it?”

Jen nodded. She couldn’t believe that he remembered this place. The meal was equally awkward, and she saw this different side to Roy. The side that his dates see. It was trippy, honestly. At the end of the meal, they walked back to her house, fairly quietly, and when they reached it, they both stood outside, wondering what the other person would do.

“Roy?”

“Yeah?”

“Never do that again.”

“What?”

“I mean, it’s not you, is it? You don’t need to be somebody else to impress me. Let’s take that off for a start.”

She gently puts her hands around his neck and takes off his tie, also unbuttoning his top button.

“I’m sorry. I just...I wanted to treat you like I would have treated any other girl.”

“You’re incredible, and weird, and funny. This stuff, we can skip this stuff, right? I know you. You know me. I know you like to play video games all day and not do your job, that you really do love your job and you’re as much of a nerd as Moss is. We don’t need to play pretend, do we Roy?”

“No, we don’t.”

“Luckily for you, I have a copy of Guitar Hero in the flat. I am going to beat you, you know that right?”

He began to giggle. So this was the same old Jen. 

“No, you’re not.”

“Yes, I am.”

“Bastard.”

The next morning, Roy began to become all too familiar with being here. Two nights in a row...Jesus. Moss would lose his mind if he knew that this was happening. Today was different. When Roy woke up, he realised that Jen must have snuck between his arms as he was sleeping and was now serving as pretty much a teddy bear. She was still asleep, and he could feel her chest rising and falling. This was better than sex, surely. He had finally found someone that he truly, truly loved. He could tell that for certain. All he did was lay back and enjoy the moment. Life was never going to get better than this.


	4. Nerds In Love

**Summary for the Chapter:**

> Moss comes back from his, um, weird honeymoon and tries to set Jen up on a date.

**Notes for the Chapter:**

> Thanks for still reading! I am warning now that there is smut in this chapter, it is labelled within the text though for all who want to avoid it. Hope you all have a good day!!!

The next few weeks were like a dream. Awkward, but a dream. It was the same, but the idea of familiarity had quickly changed into these little looks, winks when crossing each other in the corridor. And then, Jen remembered. This was the day that Moss was coming back. Luckily, they had decided to keep the pda to a minimum, and their private life hadn’t yet become that intimate. For Jen, though, it felt as if it were yesterday that she went down here for the first time. In reality, the place was horrible. But it felt like home now. Denholm always seemed so oblivious to what her skill set really was, but that was a good thing? 

As Roy was walking over in order to sort out Jen’s ‘computer’ (in reality, this usually equated to some form of flirting and the occasional kiss), suddenly the door to the office swung open. They both recognised it instantly. Moss.

“Guys! Guys! Roy, come and have a look.”

Roy apprehensively walked back into the main office, and saw it for the first time. It was a ring that looked like a circuit board. It was very Moss, everybody could agree. Jen followed, not wanting to feel left out, but felt left in the dark either way.

“I’ve missed you so much! I have so much to tell you.”

For the next few hours, all three of them sat, listening to Moss’s apparently hilarious ramblings about bad cosplayers, feeling like a grown up and how he managed to convince a five year old that his wallet was the internet. Jen tried to smile through this bit, aware that this meant she had the same technological awareness as a five year old. He seemed very happy, and even skipped through the office at one point. 

“And Jen?” Moss finally finished talking, and in her need to get him to stop, Jen silently ushered for him to continue. “I was talking to this guy, and he looked like the kind of guy you would like. You know the type. Anyway, he’s coming to your house at seven tonight.” Jen tried to smile once again, as Roy looked a little crushed. She thanked Moss through gritted teeth, returned to her office and texted Roy.

‘I don’t have to go.’  
‘You sort of do.’  
‘Food poisoning? Stuck in the toilet? Fell asleep?’  
‘I don’t want Moss to get any ideas.’  
‘He wouldn’t.’  
‘He would.’  
‘Don’t be difficult Roy.’  
‘Just go to it. I knew what we had going on was too good to be true anyways’  
‘I like it too’  
‘You don’t have to try and make me feel better’  
‘Come over at 11. He’ll be gone by then I bet’  
‘Alright’

Immediately, Jen felt guilty. It was only just starting to properly get going, that morning cuddle was about as good as it had gotten up until that point. She walked home, avoiding all of the places that she usually did. What if this guy was nice? After all this time, if two good men turned up at once, it would be her luck. This was still a different side to Roy, though. Usually he would ruin her dates. Now, he wanted her to still go to one? It felt weird, even for them and whatever this now was. Weird indeed.

At six there was a knock on the doorbell, and Jen looked at herself in the mirror before answering. Nice, but not so nice that it makes her seem too attractive to him. She answered, and a well kept man of about forty was on the other side of the door. Beside him, was a little girl, no older than five, who seemed bewildered as to why she was there.

“Oh, hi.”

“I’m really sorry. I didn’t want to cancel on somebody I didn’t know and her mother couldn’t take her. I’m Jason.”

“Jen. And who are you?” She knelt down to be on eye level with the little girl. She said Anna extremely nervously before stepping back behind her dad.

“Please, come in.”

The next few hours were the most awkward of her life. Jason spent most of his time with his daughter, understandably, and Moss’s ‘setting up’ skills were very much called into question. The time inched closer to 11pm though, and eventually Jason received a call and began to swear in the other room. Like, a lot. 

“Jen?” He asked as he walked back in, sounding extremely anxious. 

“Yeah?”

“I’ve just got a call from work. It’s urgent.”

“Excuse me?”

“I’m going to have to leave.”

“Aren’t you forgetting something?”

“Oh. Oh my god. I’m so sorry. Please, I won’t be more than an hour. Here.”

He reached into his pocket and handed her £100 before thanking her and leaving abruptly. Jen went to find Anna, who was doing her homework in Jen’s office where her dad left her. This was insane. Suddenly, the door knocked. Fuck. Even more insane. She went to the door, to find Roy, still in his uniform from work. He immediately kissed her quickly and she invited him inside. 

“So, what’s on the agenda for tonight?” Roy asked.

“There’s been a development.”

As if on cue, Anna left the bedroom, asking where her daddy was. Roy turned his gaze to Jen, and began to laugh.

“Did you steal a child?”

“Not exactly.”

After THAT conversation, the two sat on the sofa, the atmosphere could be cut with a knife. Anna sat down between the two of them, and began to giggle.

“Daddy doesn’t let me stay up this late!” She beamed in delight.

“Have you finished your homework?” Jen asked back, confused as to what devil would set a five year old homework.

“No. It’s too difficult.” 

“Let me help you.”

To Jen’s surprise, Roy moved slightly closer to Anna and opened the little book, finding the question that she couldn’t do.

“Subtraction? I find that difficult too.”

He grabbed her pencil which had found itself between the two sofa cushions and moved so that they could both see the book.

“So, What does this one say?”

“Two equals blank minus seven.”

“Right, okay. Put up two fingers for me, okay? And now, I want you to add seven to that. Yeah, like that. How many fingers do you have now?”

“Nine.”

“Exactly. Smart girl.”

Anna smiled at Roy and took her pencil back, doing a few more questions counting on her fingers like she was shown, before asking Roy to look at them, to which he put his thumbs up. Anna fell asleep soon afterwards with her head on Roy’s lap. This, again, was a new side to the man. How many different sides was this man going to have? Regardless, he also seemed tired, so Jen sat curled up reading various ridiculous sounding articles on her phone. No, she wasn’t looking for hot singles in her area. 

A massive relief came over her when Jason returned, thanking her profusely. He looked at Roy, and although a little surprised, decided not to comment, instead leading his very sleepy daughter back to the car. Shutting the door, Jen let out a massive sigh of relief.

“What asshole gives a child homework?” She heard from the other room, and began to laugh.

“I know right! She’s five.”

“Five? I don’t even remember being five.”

“Do you want a coffee?”

“Yes! That would be awesome.”

Jen made the coffee, and then returned to the sofa.

“Am I allowed to be honest with you, Roy?”

“Go ahead.”

“What do you want this to be? Honestly. I don’t care if you say that you just wanted to stay until you’ve had sex with me, but I want to know that before I get too emotionally invested in this.”

“Well,” He adjusted his collar slightly, “I want to be with you. Look at you. You’re great. And kind. And you make me happy. That’s all that should matter.”

“I make you happy?”

“You’re an idiot. And I love that.”

They both laughed, and then silence took over. It was an awkward silence, filled with this tension that neither of them could place. In some ways, it was beautiful, that moment. They made a second of eye contact, and it became abundantly clear what they were going to do.

(SMUT WARNING UNTIL END OF CHAPTER)

Jen closed the gap between the two of them, until she was sitting right next to him. For a moment, they both seemed to ponder the same question. Was this worth it? Roy looked like he was about to say something, but Jen took a deep breath and gave him a singular, soft kiss. They parted for a moment, looking into each other's eyes, before Roy pulled her back in, and the two began to kiss more passionately by the second. Soon, Jen adjusted her position on the sofa so that she was straddling Roy, and she ran her fingers through his hair as they kissed, feeling each individual strand. He parted from her lips, sucking on her neck instead, causing her to moan quietly, his hands began to rise up her shirt, reaching her bra strap. Apprehensively, he unclipped it, and Jen took off her shirt and bra at the same time. Following suit, she then pulled off his shirt, and watched Roy slowly recoil in self-consciousness.

Sensing this, she began to trace his chest with her fingertips, feeling him develop goosebumps and look at her in a strange manner.

“You look amazing.”

Without giving time for a response, Jen began to kiss him again, and she felt it for the first time. At least, it felt like it was it. Maybe it wasn’t? As he quietly moaned, she realised that it must be. Without any sort of communication, he suddenly picked her up and carried her in the same position through to the bedroom, where he placed her gently onto the bed.

“Take them off.” She ordered as seductively as she could, although she could feel her voice trembling. He obliged, showing his increasingly erect dick. He pulled her underwear off as well, showing that she was already dripping. This was the most nervous that he had ever been with a woman. He traced his finger up her opening, stopping when he reached the clit and watching it pulse under his fingertip. Then, Leaning back towards her and kissing her neck again, he slipped his fingers in, noting how wet it was as she kissed him in her pleasure. This time, it felt rougher. More like an animal. He sped up as she kissed him harder, resulting in her melting into him. When it seemed to be over, he turned his attention back to his own body, lined himself up with her, and slipped in almost effortlessly, as the two both let out a moan. She accidentally dug her nails into his back as the two continued to kiss, becoming slower towards the end and eventually, it ended and the two ended up flat on their backs next to each other, and Jen began to laugh, with it soon being the both of them.

“There’s no going back now.” She sighed, rolling over to face him as he put his arm around her shoulder and pulled her closer.

“No. No there isn’t.”


End file.
